Just because the ability to connect with a local in a new city exists, doesn't mean that the local necessarily wants to meet. This theory can be applied to many of the emerging travel tools today.
Travel startups will never emerge from the startup phase if they can't be creative and figure out a way to scale their businesses and get people to use their websites and apps more than a couple of times per year. Sometimes it means community-building or expanding beyond "travel" into local discovery.
For a travel startup like Oyster, there's nothing like attracting the interest of a deep-pocketed buyer with a huge consumer audience. Oyster knew that is what it needed and it bucked the odds and lived to fight another day.